Hooking Up

A hookup is a relationship, HOPE. It may be a short-term relationship, but it’s a relationship regardless.

And, yes, a short-term hookup can turn into a long-term relationship, HOPE, but not if you’re treating your hookups like shit (because they’re only hookups!) and not if you’re willing to let the people you hook up with treat you like shit (because you’re only a hookup). Treat your hookups like people you might actually see again—like human beings with human feelings, not just human holes and/or poles—and you might actually see them again.

You might even wind up in a long-term relationship.

Now, sometimes people hook up with strangers precisely because they wanna have sex with someone they don’t know and don’t expect to see again. And that’s not always a bad idea: Having sex with someone who you don’t expect to see again can be very liberating. A girl who can’t let herself go with a guy she’s dating—maybe she fears being slut- or nympho-shamed by a boyfriend—will grind the dick off a hookup. And it can be easier to ask someone you don’t expect to see again to do something kinky. Say a straight boy has always wanted a girl to put him in her panties and peg his ass. He could ask a girlfriend to do that for him, sure, but the stakes are higher. What if she freaks out and dumps him, and blabs to her friends—and his—about why she dumped him?

People who divide the fuckable world into those they care about (and can’t open up to sexually) and those they don’t care about (and can open up to sexually but won’t date) wind up having awesome sex with people they don’t know and lousy sex with people they marry. That’s not a good strategy for anyone interested in a successful—and sexually fulfilling—long-term relationship.

So here’s what you should do, HOPE: Be uninhibited with your hookups while treating them like people you might actually see again and insist on being treated that way in return. Don’t hook up with people who treat you like shit; don’t treat the people you hook up with like shit. Even if you know you’re not going to see someone again—maybe they’re not someone you would date or circumstances are such that you couldn’t date them even if you wanted to (business trip, European vacation, spring break, etc.)—treat your hookups with kindness, respect, and gratitude.

Finally, HOPE, some people treat hookups like shit—only after they’ve come, natch—because they want their hookups to understand that they’re not interested in a relationship. That’s not just assholery, assholes, it’s completely unnecessary assholery. If someone was kind enough to suck your dick or fuck your brains out—if someone hooked up with your ass—a little kindness and consideration isn’t too much to ask. If you’re worried that your hookup might misinterpret “kindness and consideration” for “I want to be with you forever,” tell them—gently and directly—that you’re not interested in a relationship.

Straight guy here. For the first time in my life, I am with someone who understands how much my work is a part of who I am. (I travel for research and come home and agonize over writing it up.) We have a caring and affectionate relationship. She told me at the start that she has never had an orgasm and she didn’t believe in masturbation. I knew then that the sex would be vanilla, but I didn’t realize that a year later, it would be more vanilla and less frequent. I’m going out of my mind. In the early months, we discussed open relationships. Her view was that she wasn’t interested, but if I cheated it would be fine as long as she never found out. At the time, it sounded like a trap; now it sounds like an option. Help.

Sex Too Underwhelming Can’t Kontinue

Since an honest open relationship is off the table, STUCK, I’m gonna urge you to DTMFA. (I’m not saying your girlfriend is an MF—heavens no—but DTMFA is the term of art around here.) I’m thinking you’ll have an easier time getting a girl who likes sex to understand how important your work is to you than you’ll have getting this girl to understand how important sex is to you. You and your current girlfriend simply aren’t sexually compatible, STUCK, and sexual compatibility matters when you’re picking a sex partner. Duh.

DTMFA.

I am a girl and I am stuck. My boyfriend and I have been dating for nine months, and I only recently told him I can squirt. When we would have sex before, I would tell him to stop before I came because I didn’t want to squirt. Now that he knows, he thinks it’s really hot that I can and wants me to do it. But I can’t seem to get to that point anymore. I have a vibrator, and when I masturbate, I can squirt no problem. But even with me, or him, stimulating my clit while having sex, I just can’t do it and I don’t know why.

What Should I Do?

You should relax.

I’m not saying that you’ll squirt the next time you fuck your boyfriend if you can just relax, WSID, but you’ll get there sooner if you relax about whether or not you’re squirting.

And let’s remember why you weren’t squirting with the boyfriend: You were worried that he might react negatively or think it was gross. Not squirting was something you were doing for him. Now that you know he’s into it, you want to squirt for him.

Stop thinking about him, WSID, and start thinking about yourself.

You trained your body not to come when you were with your boyfriend, and it’s going to take some time to undo that training. But if you can squirt when you masturbate alone, WSID, you can squirt with your boyfriend. And here’s how you can get there: Masturbate with your boyfriend in the house but not in your room. Then do it with him in the room but not in the bed with you—and, hey, put a blindfold on him if you’re self-conscious about him watching you. Then masturbate with him in the bed with you blindfolded. Then masturbate with him in the bed with you not blindfolded. Then masturbate with him in the bed and not blindfolded and touching you, then with him in the bed holding you, then with him in the bed helping you.

Relax, enjoy, have fun, and you’ll get there, WSID, I promise.

The advice you gave to TUSH—the gay teenager worried because he and his boyfriend weren’t any good at gay sex—isn’t exclusive to the gay young’uns. Most of us don’t start with the discipline of practice and communication often required for mutually successful sex. My first attempts, as a virgin male with a virgin female, were hilariously awkward. Nothing worked, nothing fit. Fifteen years later, with a combined 30 years of experience, we hooked up again for one of our best-ever sexual encounters. Please let the gay kids know they’re not at all alone in this crazy game of sex. Like anything worthwhile, it takes time and effort and practice to get good at it.